Pegtember: Power Shift

Oh, my husband’s asshole is so going to massively regret this.

A couple of months ago, he asked what I wanted for my birthday. I think he was thinking something nice to wear, perhaps something to show my body off, or a new sex toy or piece of kit for our sex room. What I replied was that I wanted him to complete Pegtember. He gave it a little consideration, and then said OK, if that is what I wanted. It was, and then, in a flash of inspiration and without massively thinking about it, I told him I wanted him in Girl Mode every time we pegged him, panties, skirts, costumes, that sort of thing. He looked a little wide eyed, but told me it was my birthday present, and if I wanted to peg him with him in a skirt or panties, so be it. I don’t think he really thought it through.

For those who don’t know, Pegtember is an event where someone is pegged every single day of September. Thirty consecutive peggings. Now, he’s normally pegged once a week, sometimes twice, normally Laura, Victoria and me, sometimes Carla and me, sometimes Anna and me. As you may remember, my body isn’t up to giving his ass the seeing to I think it deserves, so I get support. They get to do the long hard warm up, and I normally get to finish with the monster, the big dildo, the one that really stretches his asshole. Long satisfying pegging for him, building up through dildo sizes until I arrive with the huge one. Win-win for me, getting to watch him get near, then getting to use the huge one on him as a finale.

But a whole month. Thirty days, not missing a single session, will be hard for his ass. Mind you, I get sodomised every day, so he owes me, right?

I told the girls. I told them I needed at least one of them every single night to support me in his pegging, ideally two. I know some people do shorter peggings for Pegtember, to help the poor peggee’s asshole get through it, but I’m not. I want long, full, brutal peggings just like normal. Just more of them, just every day for a month. He’s always pushing me to take longer, harder, bigger. Now it’s his turn.

We started putting names in the calendar, and I realised I’m away working (well, fucking in the name of work) for a few days in September, so the girls agreed to peg him in my absence, live on video for me to watch and masturbate to in the comfort of my hotel room. There were lots of volunteers for pegging him, and the girls insisted on a 45 minute minimum pegging each and every day, whether I was there or not. I happily and eagerly agreed, after all it wasn’t my asshole, although I suspect my asshole will pay over the long term. It’s used to it. He’d have no choice but to agree, he’d have no choice other than to take whatever pegging we wanted to mete out.

We made up a Pegtember box for him. All the strap-on harnesses and dildos. Lube, lots and lots of lube. And women’s panties to fit him, panties I’d bought specifically for Pegtember. Proper girly panties. Tiny thongs, crotchless panties, open-backed panties, ones that wouldn’t hold his cock, thongs we would move aside to penetrate him, crotchless and open-backed ones we’d fuck through.

Also in there is a French Maid’s outfit and a Schoolgirl outfit I made for him, complete with stockings and suspenders I bought for him. I’ve been meaning to sort these outfits out for so long, and this was the excuse to get my sewing machine out. Paula and Laura wanted to peg him in a French Maid’s outfit, Anna and Victoria is a Schoolgirl one. All four will have their way. There were tiny skirts like he has me wearing, including some of the indecent variety I often wear at home, and a blouse, one for someone with tiny tits.

This Girl Mode shouldn’t be a surprise if you read my post about buying him panties and short skirts earlier in the year. He’s worn the panties a lot, and the skirts quite a bit at home, and out to the event he wanted, but I really wanted to move this on, wanted to get him into Girl Mode, which he has yet to do. This is a good chance to cement Girl Mode for him.

And also in there is a Gates of Hell cock cage with built-in Penis Plug, a stainless-steel torture device to use sometimes. Rings down the shaft, a ring round the base of his cock, a ring round the base of his balls, a ring under the edge of his Glans, and a Penis Plug, long enough so that even when he is as erect as he can be in that thing, his urethra will be full of metal. It will stop him cumming. Laura and Victoria wanted to stop him cumming. Apparently it makes the man focus on the pegging even more. And I’ve wanted one of these for him for the longest time too.

I won’t post updates every day, just occasionally. We want it to be tough for him, a struggle for him. He likes pushing us to extremes in the hunt for sexual gratification, now it’s our turn. We are going to enjoy the pegging, the costumes, the skirts, the panties, but above all, we want him to enjoy it, as well as endure it, and I want him to get really into Girl Mode and to want to do it more.

The Pegtember box is on his home office chair, waiting for him to come home from work. Laura and Victoria are due about 8pm. Let the pegging fun begin!